EP0278285A1 - Utilisation de tamis moléculaire pour la stabilisation d'esters insecticides de l'acide carbamique - Google Patents

Utilisation de tamis moléculaire pour la stabilisation d'esters insecticides de l'acide carbamique Download PDF

Info

Publication number: EP0278285A1
Authority: EP; European Patent Office
Prior art keywords: molecular sieve; acid esters; alkyl; carbamic acid; butyl
Prior art date: 1987-02-06
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

EP88100890A

Other languages

German (de)

English (en)

Inventor

Siegfried Dr. Kersten

Guenter Huber

Hans-Joachim Kuhn

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF SE

Original Assignee

BASF SE

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1987-02-06

Filing date

1988-01-22

Publication date

1988-08-17

1988-01-22 Application filed by BASF SE filed Critical BASF SE

1988-08-17 Publication of EP0278285A1 publication Critical patent/EP0278285A1/fr

Status Withdrawn legal-status Critical Current

Links

239000002808 molecular sieve Substances 0.000 title claims abstract description 35
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 title claims abstract description 35
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims abstract description 15
229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 title claims abstract description 12
230000006641 stabilisation Effects 0.000 title claims description 3
238000011105 stabilization Methods 0.000 title claims description 3
230000000749 insecticidal effect Effects 0.000 title 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 12
239000001257 hydrogen Substances 0.000 claims abstract description 8
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
229910052736 halogen Inorganic materials 0.000 claims abstract description 4
150000002367 halogens Chemical class 0.000 claims abstract description 4
150000002431 hydrogen Chemical class 0.000 claims abstract 2
230000000087 stabilizing effect Effects 0.000 claims description 6
239000011148 porous material Substances 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
239000002917 insecticide Substances 0.000 claims 1
238000000034 method Methods 0.000 claims 1
239000003381 stabilizer Substances 0.000 abstract description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
238000000354 decomposition reaction Methods 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
239000004480 active ingredient Substances 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
238000003776 cleavage reaction Methods 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
230000007017 scission Effects 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
238000009472 formulation Methods 0.000 description 2
239000011521 glass Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000000203 mixture Substances 0.000 description 2
0 *c1ccccc1O* Chemical compound *c1ccccc1O* 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
230000001133 acceleration Effects 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000000654 additive Substances 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
238000001514 detection method Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
230000004992 fission Effects 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
239000012535 impurity Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
230000002688 persistence Effects 0.000 description 1
-1 polyethylene Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
239000012808 vapor phase Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/22—O-Aryl or S-Aryl esters thereof

Definitions

the present invention relates to the use of molecular sieves for stabilizing carbamic acid esters of the general formula I.
R C1-C4 alkyl or the group means where R1 is hydrogen, halogen or C1-C4 alkyl, R2 is hydrogen or C1-C4 alkyl and R3 C1-C4 alkyl can be.
Carbamic acid esters of this type are split relatively easily by both acids and bases. In itself, this cleavage is desirable because it leads to a rapid breakdown after application of the agents (low persistence; no accumulation).
a detectable fission product is e.g. Hydrogen chloride.
the object is achieved by adding or adding molecular sieve to the carbamic acid ester I or its preparations (formulations) intended for circulation.
the substituent R in formula I has the following meanings: - C1-C4-alkyl, such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and tert-butyl, - the group in which R1 - hydrogen, Halogen, such as fluorine, chlorine or bromine, preferably chlorine, - C1-C4-alkyl, such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and tert-butyl, R2 - hydrogen, - C1-C4-alkyl, such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and tert-butyl, R3 - C1-C4-
Molecular sieve effective according to the invention has pore sizes of e.g. 0.4 to 1 mm; suitable grades of molecular sieve are commercially available.
a description of the production and mode of action and the determination of the properties of molecular sieves is e.g. O. Grübner et al, Molecular Sieves, Berlin 1968 or C.K. Hersk, Molecular Sieves, New York 1961.
the molecular sieve can be added by admixing an appropriately fine powder or, if it is a liquid preparation, also coarse pieces, spheres etc. or the molecular sieve can be added to the container separately in a permeable container, for example a small bag.
Sylosiv trademark molecular sieve was saturated over the vapor phase by allowing molecular sieve and water to separate in separate dishes in a closed vessel for 24 hours at room temperature. The molecular sieve was then kept at 45 ° C.-50 ° C. to constant weight.
a precisely weighed amount of the freshly manufactured active ingredient Ia was mixed with a precisely weighed amount of molecular sieve and mixed intensively in a glass bottle.
Sufficiently large samples (approx. 10 g) were stored in glass stopper bottles at 60 ° C, 50 ° C and room temperature. Comparative samples without addition were treated accordingly.
the samples were monitored by HPLC and GC. The results are shown in Tables 1 to 3 below.
a sample without stabilizer was stored at 60 ° C for 8 days. Decomposition products could be detected in it by gas chromatography.

Landscapes

Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

EP88100890A 1987-02-06 1988-01-22 Utilisation de tamis moléculaire pour la stabilisation d'esters insecticides de l'acide carbamique Withdrawn EP0278285A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19873703620 DE3703620A1 (de)	1987-02-06	1987-02-06	Stabilisierungsmittel fuer insektizide carbaminsaeureester
DE3703620		1987-02-06

Publications (1)

Publication Number	Publication Date
EP0278285A1 true EP0278285A1 (fr)	1988-08-17

Family

ID=6320381

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP88100890A Withdrawn EP0278285A1 (fr)	1987-02-06	1988-01-22	Utilisation de tamis moléculaire pour la stabilisation d'esters insecticides de l'acide carbamique

Country Status (3)

Country	Link
EP (1)	EP0278285A1 (fr)
JP (1)	JPS63196553A (fr)
DE (1)	DE3703620A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE69416057T2 (de) *	1993-08-31	1999-07-01	Canon K.K., Tokio/Tokyo	Mesomorphe Verbindung, eine diese enthaltene Flüssigkristallzusammensetzung, eine diese Zusammensetzung verwendende Flüssigkristallvorrichtung, Flüssigkristallapparat und Anzeigeverfahren
EP0694599B1 (fr) *	1994-07-26	2001-06-27	Canon Kabushiki Kaisha	Composition liquide cristalline, dispositif l'utilisant, appareil et méthode d'affichage
DE69618413T2 (de) *	1995-10-12	2002-06-20	Canon K.K., Tokio/Tokyo	Flüssigkristallzusammensetzung, Flüssigkristallvorrichtung und Flüssigkristallanzeigeapparat

1987
- 1987-02-06 DE DE19873703620 patent/DE3703620A1/de not_active Withdrawn
1988
- 1988-01-22 EP EP88100890A patent/EP0278285A1/fr not_active Withdrawn
- 1988-02-01 JP JP1972988A patent/JPS63196553A/ja active Pending

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Otto Grubner, Pavel Jiru und Milos Ralek "Molekularsiebe", 1968, Band 12 Veb Deutscher Verlag der Wissenschaften, Berlin seiten 71,85,88,89,99,110,111,116,117 *

Also Published As

Publication number	Publication date
JPS63196553A (ja)	1988-08-15
DE3703620A1 (de)	1988-08-18

Legal Events

Date	Code	Title	Description
1988-07-02	PUAI	Public reference made under article 153(3) epc to a published international application that has entered the european phase	Free format text: ORIGINAL CODE: 0009012
1988-08-17	17P	Request for examination filed	Effective date: 19880517
1988-08-17	AK	Designated contracting states	Kind code of ref document: A1 Designated state(s): BE CH DE FR GB IT LI NL
1989-10-04	17Q	First examination report despatched	Effective date: 19890821
1989-11-25	STAA	Information on the status of an ep patent application or granted ep patent	Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN
1990-01-03	18W	Application withdrawn	Withdrawal date: 19891110
1990-01-10	R18W	Application withdrawn (corrected)	Effective date: 19891110

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